It would be maybe 50 miles depending on point of departure and arrival. If you left early on a summer morning and managed to sustain 4 knots the whole way, you could arrive by dark. There would have to be a reasonably strong wind from the south. A tropical storm parked in the Gulf off Naples would do it.

Planning a trip across Lake Erie, myself. Departing from Erie, PA, it's about 29 miles across to the tip of Long Point peninsula on the Canadian shore. Then another 18 miles across Long Point Bay behind that, to arrive in Port Dover, Ontario. The Port Dover Yacht Club is a sister club to the yacht club I belong to in Erie, so I figured that would be a good target. I figure 10 to 14 hours on the water. Camp for a day or two over there, and then return. Since I actually live in Virginia, I have to find a time when my schedule allows me to take time off to get up to Erie, and the lake conditions line up. Couldn't find the time this past summer, but I'm hoping for next. The call to Canadian customs & immigration when I get over there ought to be interesting. "You came over HOW?"

You know that run from FLM to Chok is a leg (in reverse) of the WaterTribe Everglades Challenge. I think doing it in one day solo would be a record of some sort. It might not stand long, but I think it would be a record. If I added "age" qualification to the record, it might stand for some time.

IN the late 70's I sailed a Hobie 16 a lot and I always heard about a guy who did it in a Hobie 14. That was in the days before internet so hard to dig up or confirm now, but all this adventure talk brought it to mind again.